Aside from its deep-rooted history, on the water activities, dining options, and thriving arts and culture scene, Annapolis and Anne Arundel County is a great place to shop. Whether you’re looking for a little Chesapeake style for a new summer wardrobe or seeking that eye-catching piece from an antique store, Annapolis has much to offer. For your convenience, we’ve put together this seasonal shopping guide to help you next time you’re in the area.

Fall/Winter Shopping

With the holiday season coming up quickly, it’s time to start shopping. In Annapolis, you’ll find all the name brands you love at the Annapolis Towne Centre and Westfield Annapolis Mall. Only a short drive up West Street, these two shopping centers offer customers all the products they want at bargain prices – perfect for the holiday shopping list. 

Another great option to get your holiday shopping completed is the Arundel Mills Mall. With over 200 stores on location, Arundel Mills is the state’s largest outlet mall. The outlet holds sales year-round, but the deals pick up during the holiday season, making for a great way to get all of your shopping knocked out in one trip. 

Spring Shopping

After the cold of winter subsides, Annapolis’ walkable charm returns to town, making for the perfect time to get some shopping done in historic downtown. On Main Street, you’ll find everything from children's stores and sailing outfitters to jewelry shops and gift stores. If you’re looking for a new spring outfit, there’s also dozens of boutique and specialty shops offering that Chesapeake allure you’re after. You’ll find plenty of restaurants on Main Street as well, ideal for a mid-day break from your shopping spree.

Maryland Avenue is another great option for shoppers in downtown Annapolis. Known as the oldest retail-affiliated road in Maryland, Maryland Avenue is lined with boutique and gift shops, apparel stores, galleries, two antique stores, and a bookstore. It’s also down the road from the United States Naval Academy where you can take a tour of the “Yard.”

If you're looking for more, head across the bridge from downtown over to Eastport. Here, you’ll find more antiques jam-packed with maritime-themed pieces, along with art galleries and great restaurants. There’s also West Annapolis, boasting a number of antique shops and boutiques. The best part? Each area is only a short walk from one another. 

Summer Shopping

All of Annapolis is in full swing when the summer rolls around. For the art lover, that means walking from one gallery to another. With over 25 art galleries in town, Annapolis offers a little something for any art enthusiast: sculpture, paintings, ceramic, glasswork. Start on West Street in the Arts District where you’ll find a number of art galleries lining the road before heading over to Main Street, home to some of the city’s favorite galleries.

After Main Street, head back up the hill to State Circle, where you’ll find the Maryland Federation of Art (aka Circle Gallery). Here, you’ll find exhibits from all over the world as well as art for sale. Make your way around the State House and head down Maryland Avenue where there’s two more great galleries offering fine art to add to your collections.

Want to find out more about all the great shopping option available in Annapolis and Anne Arundel County? Click here for a full list of stores in the area.